#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239113.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2239113
loop_
_publ_author_name
'Oulemda, Bassou'
'Rakib, El Mostapha'
'Abbassi, Najat'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
1-(4-Methylphenylsulfonyl)-5,6-dinitro-1H-indazole
;
_journal_coeditor_code BT6953
_journal_issue 1
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o101
_journal_paper_doi 10.1107/S1600536813034326
_journal_volume 70
_journal_year 2014
_chemical_formula_iupac 'C14 H10 N4 O6 S'
_chemical_formula_moiety 'C14 H10 N4 O6 S'
_chemical_formula_sum 'C14 H10 N4 O6 S'
_chemical_formula_weight 362.32
_chemical_name_systematic
;
1-(4-Methylphenylsulfonyl)-5,6-dinitro-1H-indazole
;
_space_group_IT_number 2
_symmetry_cell_setting triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.401(2)
_cell_angle_beta 95.707(2)
_cell_angle_gamma 111.302(2)
_cell_formula_units_Z 2
_cell_length_a 7.4125(3)
_cell_length_b 8.5371(3)
_cell_length_c 13.0825(5)
_cell_measurement_reflns_used 3383
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 27.09
_cell_measurement_theta_min 2.56
_cell_volume 766.66(5)
_computing_cell_refinement 'SAINT (Bruker, 2009)'
_computing_data_collection 'APEX2 (Bruker, 2009)'
_computing_data_reduction 'SAINT (Bruker, 2009)'
_computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker X8 APEX'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0306
_diffrn_reflns_av_sigmaI/netI 0.0186
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 19101
_diffrn_reflns_theta_full 27.09
_diffrn_reflns_theta_max 27.09
_diffrn_reflns_theta_min 2.56
_exptl_absorpt_coefficient_mu 0.254
_exptl_absorpt_correction_T_max 0.7466
_exptl_absorpt_correction_T_min 0.6934
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2009)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.570
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description Block
_exptl_crystal_F_000 372
_exptl_crystal_size_max 0.42
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.28
_refine_diff_density_max 0.461
_refine_diff_density_min -0.317
_refine_ls_extinction_coef 0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.068
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 227
_refine_ls_number_reflns 3383
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.068
_refine_ls_R_factor_all 0.0475
_refine_ls_R_factor_gt 0.0423
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0641P)^2^+0.3549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1188
_refine_ls_wR_factor_ref 0.1246
_reflns_number_gt 2984
_reflns_number_total 3383
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL EL13_D526_BO37 in P-1
CELL 0.71073 7.4125 8.5371 13.0825 90.401 95.707 111.302
ZERR 2.00 0.0003 0.0003 0.0005 0.002 0.002 0.002
LATT 1
SFAC C H N O S
UNIT 28 20 8 12 2
MERG 2
SHEL 60 0.78
OMIT 0 0 1
ACTA
FMAP 2
PLAN 10
BOND
BOND $H
HTAB 2.6
EQIV $1 x-1, y, z
HTAB C5 O5_$1
L.S. 10
TEMP 23.00
size 0.41 0.36 0.21
WGHT 0.0641 0.3549
EXTI 0.022587
FVAR 0.90785
C1 1 0.024870 0.141374 0.350233 11.00000 0.03848 0.03057 =
0.02825 0.00197 0.00302 0.01455
C2 1 0.158780 0.233764 0.432020 11.00000 0.03797 0.03815 =
0.03247 -0.00075 -0.00077 0.01402
AFIX 43
H2 2 0.292358 0.263213 0.431234 11.00000 -1.20000
AFIX 0
C3 1 0.081377 0.278222 0.513283 11.00000 0.04868 0.03111 =
0.03007 0.00020 0.00041 0.01445
C4 1 -0.120934 0.232585 0.515640 11.00000 0.05400 0.03484 =
0.03287 0.00520 0.01280 0.02001
C5 1 -0.251047 0.142193 0.435474 11.00000 0.04001 0.04104 =
0.03961 0.00595 0.00961 0.01596
AFIX 43
H5 2 -0.384471 0.112146 0.437277 11.00000 -1.20000
AFIX 0
C6 1 -0.176834 0.096525 0.350818 11.00000 0.03567 0.03262 =
0.03372 0.00376 0.00280 0.01260
C7 1 -0.259939 0.012009 0.253440 11.00000 0.03591 0.04228 =
0.03843 -0.00092 -0.00121 0.01120
AFIX 43
H7 2 -0.392909 -0.031656 0.232175 11.00000 -1.20000
AFIX 0
C8 1 0.259198 0.283472 0.120625 11.00000 0.03159 0.04088 =
0.03218 -0.00236 0.00526 0.01569
C9 1 0.310048 0.444927 0.164441 11.00000 0.05154 0.04537 =
0.03957 -0.00728 0.00192 0.01716
AFIX 43
H9 2 0.346539 0.466884 0.234718 11.00000 -1.20000
AFIX 0
C10 1 0.304684 0.571466 0.100445 11.00000 0.05745 0.04195 =
0.06425 0.00146 0.01021 0.01917
AFIX 43
H10 2 0.335565 0.679570 0.128612 11.00000 -1.20000
AFIX 0
C11 1 0.254508 0.541450 -0.004548 11.00000 0.03711 0.06038 =
0.05809 0.02077 0.01834 0.02296
C12 1 0.205985 0.379217 -0.045507 11.00000 0.05153 0.07505 =
0.03511 0.00919 0.00924 0.02766
AFIX 43
H12 2 0.172519 0.357807 -0.116011 11.00000 -1.20000
AFIX 0
C13 1 0.206375 0.249047 0.016224 11.00000 0.04754 0.05151 =
0.03221 -0.00607 0.00568 0.01929
AFIX 43
H13 2 0.171811 0.140367 -0.011818 11.00000 -1.20000
AFIX 0
C14 1 0.250599 0.682208 -0.072821 11.00000 0.06253 0.08890 =
0.09388 0.05036 0.03366 0.04208
AFIX 33
H14A 2 0.366194 0.779808 -0.055003 11.00000 -1.50000
H14B 2 0.138000 0.708926 -0.063518 11.00000 -1.50000
H14C 2 0.245117 0.647425 -0.143369 11.00000 -1.50000
AFIX 0
N1 3 0.222902 0.372202 0.599839 11.00000 0.06502 0.04461 =
0.03549 -0.00756 -0.00277 0.01685
N2 3 -0.197546 0.294359 0.600159 11.00000 0.07173 0.05475 =
0.04182 0.00285 0.02049 0.02815
N3 3 -0.127784 0.003282 0.197981 11.00000 0.04149 0.04075 =
0.03320 -0.00401 -0.00269 0.01295
N4 3 0.048932 0.078378 0.257535 11.00000 0.03605 0.04085 =
0.02978 -0.00401 0.00152 0.01267
O1 4 0.350628 0.501391 0.580783 11.00000 0.08982 0.08587 =
0.06804 -0.02158 -0.00053 -0.01713
O2 4 0.209069 0.312225 0.682518 11.00000 0.13830 0.07760 =
0.03869 0.00195 -0.01838 0.03754
O3 4 -0.094920 0.430868 0.642454 11.00000 0.10320 0.06464 =
0.06961 -0.01760 0.02451 0.03147
O4 4 -0.360704 0.214639 0.618391 11.00000 0.09302 0.09524 =
0.08671 -0.01139 0.05686 0.01302
O5 4 0.405673 0.178798 0.284035 11.00000 0.04033 0.06914 =
0.04383 0.00180 -0.00167 0.02887
O6 4 0.230494 -0.027528 0.140449 11.00000 0.07010 0.04856 =
0.05426 -0.00485 0.01368 0.03389
S1 5 0.256243 0.119853 0.200186 11.00000 0.03944 0.04347 =
0.03487 -0.00191 0.00423 0.02274
HKLF 4
REM EL13_D526_BO37 in P-1
REM R1 = 0.0423 for 2984 Fo > 4sig(Fo) and 0.0475 for all 3383 data
REM 227 parameters refined using 0 restraints
END
WGHT 0.0641 0.3549
REM Highest difference peak 0.461, deepest hole -0.317, 1-sigma level 0.053
Q1 1 0.1618 0.5043 0.6268 11.00000 0.05 0.46
Q2 1 0.3367 0.3403 0.6348 11.00000 0.05 0.45
Q3 1 -0.1714 0.2434 0.6874 11.00000 0.05 0.42
Q4 1 -0.1033 0.3100 0.6818 11.00000 0.05 0.32
Q5 1 0.2643 0.2236 0.1565 11.00000 0.05 0.31
Q6 1 0.2634 0.3544 0.1443 11.00000 0.05 0.24
Q7 1 -0.0865 0.1069 0.3584 11.00000 0.05 0.24
Q8 1 0.3568 0.7150 -0.1186 11.00000 0.05 0.23
Q9 1 0.2410 0.2684 0.0765 11.00000 0.05 0.22
Q10 1 0.1030 0.6416 -0.1174 11.00000 0.05 0.22
;
_cod_data_source_file bt6953sup1.cif
_cod_data_source_block I
_cod_database_code 2239113
_cod_database_fobs_code 2239113
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.0249(2) 0.1414(2) 0.35023(12) 0.0319(3) Uani d . 1 1
C C2 0.1588(3) 0.2338(2) 0.43202(13) 0.0365(4) Uani d . 1 1
H H2 0.2924 0.2632 0.4312 0.044 Uiso calc R 1 1
C C3 0.0814(3) 0.2782(2) 0.51328(13) 0.0370(4) Uani d . 1 1
C C4 -0.1209(3) 0.2326(2) 0.51564(13) 0.0389(4) Uani d . 1 1
C C5 -0.2510(3) 0.1422(2) 0.43547(14) 0.0395(4) Uani d . 1 1
H H5 -0.3845 0.1121 0.4373 0.047 Uiso calc R 1 1
C C6 -0.1768(2) 0.0965(2) 0.35082(13) 0.0340(4) Uani d . 1 1
C C7 -0.2599(3) 0.0120(2) 0.25344(14) 0.0401(4) Uani d . 1 1
H H7 -0.3929 -0.0317 0.2322 0.048 Uiso calc R 1 1
C C8 0.2592(2) 0.2835(2) 0.12063(13) 0.0341(4) Uani d . 1 1
C C9 0.3100(3) 0.4449(2) 0.16444(15) 0.0459(4) Uani d . 1 1
H H9 0.3465 0.4669 0.2347 0.055 Uiso calc R 1 1
C C10 0.3047(3) 0.5715(3) 0.10045(19) 0.0540(5) Uani d . 1 1
H H10 0.3356 0.6796 0.1286 0.065 Uiso calc R 1 1
C C11 0.2545(3) 0.5414(3) -0.00455(17) 0.0494(5) Uani d . 1 1
C C12 0.2060(3) 0.3792(3) -0.04551(16) 0.0523(5) Uani d . 1 1
H H12 0.1725 0.3578 -0.1160 0.063 Uiso calc R 1 1
C C13 0.2064(3) 0.2490(3) 0.01622(14) 0.0434(4) Uani d . 1 1
H H13 0.1718 0.1404 -0.0118 0.052 Uiso calc R 1 1
C C14 0.2506(4) 0.6822(4) -0.0728(2) 0.0757(8) Uani d . 1 1
H H14A 0.3662 0.7798 -0.0550 0.114 Uiso calc R 1 1
H H14B 0.1380 0.7089 -0.0635 0.114 Uiso calc R 1 1
H H14C 0.2451 0.6474 -0.1434 0.114 Uiso calc R 1 1
N N1 0.2229(3) 0.3722(2) 0.59984(13) 0.0499(4) Uani d . 1 1
N N2 -0.1975(3) 0.2944(2) 0.60016(14) 0.0537(5) Uani d . 1 1
N N3 -0.1278(2) 0.00328(19) 0.19798(11) 0.0396(3) Uani d . 1 1
N N4 0.0489(2) 0.07838(19) 0.25754(11) 0.0361(3) Uani d . 1 1
O O1 0.3506(3) 0.5014(3) 0.58078(16) 0.0959(8) Uani d . 1 1
O O2 0.2091(4) 0.3122(3) 0.68252(13) 0.0874(7) Uani d . 1 1
O O3 -0.0949(3) 0.4309(2) 0.64245(15) 0.0780(6) Uani d . 1 1
O O4 -0.3607(3) 0.2146(3) 0.61839(17) 0.0944(7) Uani d . 1 1
O O5 0.4057(2) 0.1788(2) 0.28403(11) 0.0491(4) Uani d . 1 1
O O6 0.2305(2) -0.02753(18) 0.14045(12) 0.0538(4) Uani d . 1 1
S S1 0.25624(6) 0.11985(6) 0.20019(3) 0.03714(16) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0385(8) 0.0306(8) 0.0282(8) 0.0145(7) 0.0030(6) 0.0020(6)
C2 0.0380(9) 0.0381(9) 0.0325(8) 0.0140(7) -0.0008(7) -0.0007(7)
C3 0.0487(10) 0.0311(8) 0.0301(8) 0.0145(7) 0.0004(7) 0.0002(6)
C4 0.0540(11) 0.0348(9) 0.0329(9) 0.0200(8) 0.0128(8) 0.0052(7)
C5 0.0400(9) 0.0410(9) 0.0396(9) 0.0160(8) 0.0096(7) 0.0059(7)
C6 0.0357(8) 0.0326(8) 0.0337(8) 0.0126(7) 0.0028(7) 0.0038(6)
C7 0.0359(9) 0.0423(9) 0.0384(9) 0.0112(7) -0.0012(7) -0.0009(7)
C8 0.0316(8) 0.0409(9) 0.0322(8) 0.0157(7) 0.0053(6) -0.0024(7)
C9 0.0515(11) 0.0454(10) 0.0396(10) 0.0172(9) 0.0019(8) -0.0073(8)
C10 0.0575(13) 0.0419(11) 0.0643(14) 0.0192(9) 0.0102(11) 0.0015(10)
C11 0.0371(10) 0.0604(12) 0.0581(12) 0.0230(9) 0.0183(9) 0.0208(10)
C12 0.0515(11) 0.0751(14) 0.0351(10) 0.0277(11) 0.0092(8) 0.0092(9)
C13 0.0475(10) 0.0515(11) 0.0322(9) 0.0193(9) 0.0057(8) -0.0061(8)
C14 0.0625(15) 0.0889(19) 0.094(2) 0.0421(14) 0.0337(14) 0.0504(16)
N1 0.0650(11) 0.0446(9) 0.0355(9) 0.0168(8) -0.0028(8) -0.0076(7)
N2 0.0717(12) 0.0547(10) 0.0418(9) 0.0282(9) 0.0205(9) 0.0028(8)
N3 0.0415(8) 0.0407(8) 0.0332(8) 0.0129(7) -0.0027(6) -0.0040(6)
N4 0.0360(7) 0.0409(8) 0.0298(7) 0.0127(6) 0.0015(6) -0.0040(6)
O1 0.0898(15) 0.0859(14) 0.0680(12) -0.0171(12) -0.0005(11) -0.0216(11)
O2 0.1383(19) 0.0776(12) 0.0387(9) 0.0375(13) -0.0184(10) 0.0019(8)
O3 0.1032(15) 0.0646(11) 0.0696(11) 0.0315(10) 0.0245(11) -0.0176(9)
O4 0.0930(15) 0.0952(15) 0.0867(14) 0.0130(12) 0.0569(13) -0.0114(12)
O5 0.0403(7) 0.0691(9) 0.0438(7) 0.0289(7) -0.0017(6) 0.0018(7)
O6 0.0701(10) 0.0486(8) 0.0543(9) 0.0339(7) 0.0137(7) -0.0048(7)
S1 0.0394(3) 0.0435(3) 0.0349(2) 0.0227(2) 0.00423(18) -0.00191(18)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N4 C1 C2 132.03(16)
N4 C1 C6 105.65(15)
C2 C1 C6 122.32(16)
C3 C2 C1 116.04(16)
C3 C2 H2 122.0
C1 C2 H2 122.0
C2 C3 C4 122.37(16)
C2 C3 N1 115.68(17)
C4 C3 N1 121.92(16)
C5 C4 C3 121.29(16)
C5 C4 N2 117.78(18)
C3 C4 N2 120.69(17)
C4 C5 C6 117.80(17)
C4 C5 H5 121.1
C6 C5 H5 121.1
C5 C6 C1 120.16(16)
C5 C6 C7 134.80(17)
C1 C6 C7 105.00(15)
N3 C7 C6 111.90(16)
N3 C7 H7 124.1
C6 C7 H7 124.1
C13 C8 C9 121.71(18)
C13 C8 S1 119.26(14)
C9 C8 S1 119.01(14)
C10 C9 C8 118.03(18)
C10 C9 H9 121.0
C8 C9 H9 121.0
C9 C10 C11 121.7(2)
C9 C10 H10 119.2
C11 C10 H10 119.2
C10 C11 C12 118.67(19)
C10 C11 C14 120.6(2)
C12 C11 C14 120.8(2)
C13 C12 C11 121.32(19)
C13 C12 H12 119.3
C11 C12 H12 119.3
C12 C13 C8 118.61(19)
C12 C13 H13 120.7
C8 C13 H13 120.7
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O2 N1 O1 124.8(2)
O2 N1 C3 118.03(18)
O1 N1 C3 117.08(18)
O4 N2 O3 124.3(2)
O4 N2 C4 118.2(2)
O3 N2 C4 117.26(19)
C7 N3 N4 106.16(14)
C1 N4 N3 111.21(14)
C1 N4 S1 128.92(12)
N3 N4 S1 118.15(11)
O6 S1 O5 121.02(9)
O6 S1 N4 106.26(8)
O5 S1 N4 103.11(8)
O6 S1 C8 110.38(9)
O5 S1 C8 110.65(9)
N4 S1 C8 103.62(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N4 1.377(2)
C1 C2 1.400(2)
C1 C6 1.403(2)
C2 C3 1.370(2)
C2 H2 0.9300
C3 C4 1.409(3)
C3 N1 1.472(2)
C4 C5 1.368(3)
C4 N2 1.469(2)
C5 C6 1.397(2)
C5 H5 0.9300
C6 C7 1.425(2)
C7 N3 1.298(2)
C7 H7 0.9300
C8 C13 1.382(2)
C8 C9 1.392(3)
C8 S1 1.7429(18)
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.384(3)
C10 H10 0.9300
C11 C12 1.387(3)
C11 C14 1.509(3)
C12 C13 1.379(3)
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 O2 1.198(2)
N1 O1 1.211(3)
N2 O4 1.202(3)
N2 O3 1.227(3)
N3 N4 1.383(2)
N4 S1 1.6992(15)
O5 S1 1.4245(14)
O6 S1 1.4186(14)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O5 1_455 0.93 2.61 3.175(2) 119.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086374